CN101273097B - Method of preparing pigment compositions - Google Patents

Method of preparing pigment compositions Download PDF

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Publication number
CN101273097B
CN101273097B CN2006800351660A CN200680035166A CN101273097B CN 101273097 B CN101273097 B CN 101273097B CN 2006800351660 A CN2006800351660 A CN 2006800351660A CN 200680035166 A CN200680035166 A CN 200680035166A CN 101273097 B CN101273097 B CN 101273097B
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pigment
polymkeric substance
color compositions
preparation
described color
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CN101273097A (en
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保罗·S·帕伦博
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Cabot Corp
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Cabot Corp
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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D11/00—Inks
    • C09D11/30—Inkjet printing inks
    • C09D11/32—Inkjet printing inks characterised by colouring agents
    • C09D11/322—Pigment inks
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/006—Preparation of organic pigments
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0071—Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
    • C09B67/0084—Dispersions of dyes
    • C09B67/0085—Non common dispersing agents
    • C09B67/009—Non common dispersing agents polymeric dispersing agent
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09C—TREATMENT OF INORGANIC MATERIALS, OTHER THAN FIBROUS FILLERS, TO ENHANCE THEIR PIGMENTING OR FILLING PROPERTIES ; PREPARATION OF CARBON BLACK  ; PREPARATION OF INORGANIC MATERIALS WHICH ARE NO SINGLE CHEMICAL COMPOUNDS AND WHICH ARE MAINLY USED AS PIGMENTS OR FILLERS
    • C09C3/00—Treatment in general of inorganic materials, other than fibrous fillers, to enhance their pigmenting or filling properties
    • C09C3/10—Treatment with macromolecular organic compounds
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D11/00—Inks
    • C09D11/30—Inkjet printing inks
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D11/00—Inks
    • C09D11/30—Inkjet printing inks
    • C09D11/32—Inkjet printing inks characterised by colouring agents
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D11/00—Inks
    • C09D11/30—Inkjet printing inks
    • C09D11/32—Inkjet printing inks characterised by colouring agents
    • C09D11/324—Inkjet printing inks characterised by colouring agents containing carbon black
    • C09D11/326—Inkjet printing inks characterised by colouring agents containing carbon black characterised by the pigment dispersant
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D17/00—Pigment pastes, e.g. for mixing in paints

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Dispersion Chemistry (AREA)
  • Inks, Pencil-Leads, Or Crayons (AREA)
  • Pigments, Carbon Blacks, Or Wood Stains (AREA)

Abstract

The present invention relates to a method of preparing a pigment composition comprising the steps of combining a polymer and a pigment to form a mixture and heating the mixture to a temperature of between about 70 DEG C. and 25O DEG C. to form the pigment composition. The method may further comprise the step of dispersing the pigment composition in an aqueous medium to form an aqueous pigment dispersion. The pigment compositions and aqueous pigment compositions can be used in an inkjet ink composition, which is also disclosed.

Description

The method for preparing color compositions
Technical field
The present invention relates to color compositions, for the preparation of the method for color compositions, and the water dispersion and the inkjet ink composition that comprise these color compositions.
Background technology
Inkjet ink composition is generally by forming as the vehicle of carrier and tinting material such as dyestuff or pigment.Additive and/or solubility promoter also can introduce to regulate jetted ink, realize required overall performance.
Usually, pigment is not easy separately to be dispersed in the liquid vehicle.Developed various technology, it can provide the stable pigment dispersion that can be used for ink jet printing.For example, dispersion agent can add pigment to improve its dispersiveness in particular medium.The example of dispersion agent comprises water-soluble polymers and tensio-active agent.Usually, the molecular weight of these polymeric dispersants is lower than 20,000 to keep solubleness and therefore to keep pigment stability.
The surface of pigment comprises various functional group and the type of the group that exists depends on the concrete kind of pigment.Developed be used to the some methods that graft materials and, in particular, polymers on these surface of pigments.For example, shown that polymkeric substance can be connected on the carbon black that comprises surface group such as phenol and carboxyl.But the method that depends on the intrinsic functionality of surface of pigments can not widespread use, because not every pigment has identical particular functional group.
Also developed the method for the preparation of the pigment products of modification, it can provide the pigment of the functional group with various connection.For example, U.S. Patent No. 5,851,280 disclose for the method that organic group is connected on the pigment, and this connection for example comprises and connecting by the diazonium salt reaction that wherein organic group is the part of diazonium salt.
Other method of the pigment (pigment that comprises the polymeric groups with connection) of preparation modification has also been described.For example, the open No.WO01/51566 of PCT discloses by first chemical group and the reaction of second chemical group are formed the method that the pigment that is connected with the 3rd chemical group is made the pigment of modification.Also describe the ink composite that comprises these pigment, comprised jetted ink.In addition, U.S. Patent No. 5,698,016 discloses a kind of composition that comprises amphiphilic ions and modified carbon products, and described modified carbon products comprises the carbon that is connected with at least one organic group.Described organic group has the electric charge opposite with amphiphilic ions.Also disclose moisture and non-aqueous ink and the coating composition of introducing said composition, comprised inkjet ink composition.In addition, polymer coated carbon products and its preparation method are described in U.S. Patent No. 6,458, in 458.
Although these methods provide the modified pigment with linking group, but still need to improve for the preparation of color compositions, especially comprise the method for compositions of polymkeric substance, the favourable replacement method that forms modified pigment is provided thus.
Summary of the invention
The present invention relates to a kind of method for preparing color compositions, comprise with polymkeric substance and pigment combinations with form mixture and this mixture of heating to about 70 ℃-250 ℃ temperature to form the step of color compositions.Preferably, polymkeric substance comprises the ammonium salt of at least a hydroxy-acid group.The color compositions that is obtained by this method is also disclosed.
The invention further relates to a kind of method for preparing aqueous pigment dispersions, comprise that forming color compositions as described herein also is dispersed in this color compositions in the water to form the step of aqueous pigment dispersions.The aqueous pigment dispersions that is obtained by this method is also disclosed.
The invention further relates to a kind of inkjet ink composition, comprise liquid vehicle and color compositions as herein described or comprise the aqueous pigment dispersions of color compositions as herein described.Preferably, to use method as herein described preparation and liquid vehicle be aqueous vehicle for color compositions and aqueous pigment dispersions.
Should be understood that above general introduction and following detailed description only for exemplary and indicative, and be used for providing further explanation to the present invention for required protection.
Embodiment
The present invention relates to the method for the preparation of color compositions and aqueous pigment dispersions, and relate to color compositions and the aqueous pigment dispersions of gained and further relate to the inkjet ink composition that comprises them.
The inventive method comprises polymkeric substance and pigment combinations to form the step of mixture.The gained mixture with post-heating to form polymer composition.In preferred embodiments, the inventive method further comprises polymer composition is dispersed in the water medium to form the step of aqueous pigment dispersions.In these steps of following more detailed description each.
In the methods of the invention, polymkeric substance and pigment combinations are to form mixture.Polymkeric substance is preferably water-soluble polymers, as comprise polyalkylene oxide groups polymkeric substance, comprise quaternary ammonium group polymkeric substance, comprise the group that obtains by the hydrolysis subsequently of vinyl acetate polyisocyanate polyaddition polymkeric substance (as polyvinyl alcohol), comprise the polymkeric substance (as the poly-N-vinyl pyrrolidone) of the group that the polymerization by vinyl pyrrolidone obtains and comprise the polymkeric substance of at least a acid groups or its salt, acid groups such as sulfonic acid group or hydroxy-acid group, salt comprise sodium, potassium and ammonium salt.The salt that most preferably comprises at least a hydroxy-acid group, the polymkeric substance of the ammonium salt of especially at least a hydroxy-acid group.For this preferred embodiment, can use any polymkeric substance with this group, for example comprise the polymkeric substance of the polymkeric substance of the monomer polymerization preparation by comprising hydroxy-acid group or its salt and the monomer polymerization preparation by comprising the group that can change into hydroxy-acid group or its salt.Polymkeric substance can be to comprise homopolymer or the multipolymer of ammonium carboxylate groups and can be unregulated polymer, alternating polymer, graftomer, block polymer, star-shape polymer and/or comb-shaped polymer.Preferably, polymkeric substance comprises the ammonium carboxylate groups of at least 10% weight, more preferably at least 20% weight and most preferably at least 30% weight.Polymkeric substance also can comprise multiple hydroxy-acid group, and wherein at least a is the form of ammonium salt.The example that can be used for the polymkeric substance of the inventive method includes, but not limited to ammonium acrylate or methacrylate polymers, as styrene-propene acid ammonium or vinylbenzene-ammonio methacrylate copolymer.
The molecular weight of polymkeric substance can change according to various factors.For example, the form of the viscosity of the solubleness of polymericular weight impact polymer, gained solution and polymkeric substance (solid, wax, thick liquid or free flowing liquid).Used mixing or heating condition in the inventive method in greater detail below this also can influence.Preferably, it is about 20,000 that the molecular weight of polymkeric substance is lower than, and according to appointment 2,000 to 15,000, more preferably from about 5,000 to 12,000 and most preferably from about 8,000 to 10,000.
Pigment can be the pigment of the normally used any kind of those skilled in the art, as black pigment and other coloured pigment, comprises blueness, black, brown, cyan, green, white, purple, magenta, redness, orange or yellow ultramarine.The mixture of different pigment also can use.The representative example of charcoal blacks comprises various carbon blacks (Pigment black 7) as thermally oxidized black, furnace black and dim, and for example comprise with
Figure GSB00001072687200031
With
Figure GSB00001072687200032
Trade mark available from the carbon black of Cabot Corporation (as Black
Figure GSB00001072687200033
2000, Black
Figure GSB00001072687200034
1400, Black
Figure GSB00001072687200035
1300, Black
Figure GSB00001072687200036
1100, Black
Figure GSB00001072687200037
1000, Black 900, Black 880, Black
Figure GSB000010726872000310
800, Black
Figure GSB000010726872000311
700, Black
Figure GSB000010726872000312
L,
Figure GSB000010726872000313
8,
Figure GSB000010726872000314
1400,
Figure GSB000010726872000315
1300,
Figure GSB000010726872000316
1100,
Figure GSB000010726872000317
1000, 900,
Figure GSB000010726872000319
880,
Figure GSB000010726872000320
800,
Figure GSB000010726872000321
700,
Figure GSB000010726872000322
L,
Figure GSB000010726872000323
330,
Figure GSB000010726872000324
400,
Figure GSB000010726872000325
P).The coloured pigment of suitable species comprises, for example, and anthraquinone, phthalocyanine blue, phthalocyanine green, diazonium, monoazo, pyranthrone, perylene, heterocyclic yellows, quinacridone and (sulfo-) indigoid dye.These pigment are purchased with powder or cake form takes pride in multi-source, comprises BASF Corporation, Engelhard Corporation and Sun Chemical Corporation.The example of the coloured pigment that other is suitable is described in color index, the third edition (dyestuff scholar and pigment scholar association, 1982) (Color Index, 3rd edition (The Society ofDyers and Colourists, 1982)).Preferably, pigment is cyan, magenta, yellow or black pigment such as carbon black.
The desired properties that depends on pigment, pigment can have the BET surface-area of wide region, and it is by the nitrogen determining adsorption.As well known by persons skilled in the art, high surface area is corresponding to smaller particle size.If high surface area is not easy to obtain for required application, those skilled in the art also will appreciate that, if desired, pigment can carry out that stock size reduces or crushing technology such as ball milling or jet grinding, so that pigment is decreased to than small particle size.
Pigment can also be the modified pigment that comprises any above-mentioned pigment.For example, the pigment of modification can comprise the pigment with connection at least one ionic group, ionogen or its mixture.Example comprises and uses the oxygenant oxidation so that ion and/or ionogen are introduced lip-deep pigment.The modified pigment of direction preparation like this has the oxy radical of higher degree from the teeth outwards.Oxygenant comprises, but be not limited to, oxygen, ozone, superoxide such as hydrogen peroxide, persulphate comprise Sodium Persulfate and potassium, inferior rock salt such as clorox, oxidizing acid such as nitric acid and contain oxygenant such as permanganate, perosmic anhydride, chromic oxide or the ceric ammonium nitrate of transition metal.Also can use the mixture of oxygenant, especially the mixture of gaseous oxidizer such as oxygen and ozone.Also can use ion or ionogen are incorporated into other surface modifying method on the surface of pigments, as chlorination and sulfonylation.
In addition, modified pigment can comprise the pigment that is connected with at least one organic group, and wherein organic group comprises at least one ionic group, at least one ionogen or its mixture.These modified pigments can use any method preparation well known by persons skilled in the art, make the organic chemistry group be connected on the pigment.For example, modified pigment can use and be described in U.S. Patent No. 5,554,739,5,707,432,5,837,045,5,851,280,5,885,335,5,895,522,5,900,029,5,922,118 and 6,042,643 and the method preparation of the open WO99/23174 of PCT, its specification sheets is incorporated the present invention into as a reference fully at this.Compare with the dispersion formulation method of using polymkeric substance for example and/or tensio-active agent, thisly provide the more stable connection of group on pigment.
Ionic group can be negatively charged ion or positively charged ion and associate with the counter ion of opposite charges, comprise inorganic or means organic balance ion such as Na +, K +, Li +, NH 4 +, NR ' 4 +, acetate moiety, NO 3 -, SO 4 -2, R ' SO 3 -, R ' OSO 3 -, OH -And Cl -, wherein R ' expression hydrogen or organic group as replace or unsubstituted aryl and/or alkyl group.Ionogen can form those of ionic group in working medium.But anionizable group forms negatively charged ion and cationizable groups forms positively charged ion.Preferably, the group of connection is organic group.The organic ion group comprises and is described in U.S. Patent No. 5,698, those of 016, and this incorporates the present invention as a reference fully into its specification sheets.
Anionic group is electronegative ionic group, and it can generate by having ionizable substituting group such as the substituent group of acidity (but anionizable group) that can form negatively charged ion.They can also be the negatively charged ion in the substituent salt of ionizable.The representative example of anionic group comprises-COO -,-SO 3 -,-DSO 3 -,-HPO 3 -,-OPO 3 -2, and-PO 3 -2But the representative example of anionizable group comprises-COOH ,-SO 3H ,-PO 3H 2,-R ' SH ,-R ' OH and-SO 2NHCOR ', wherein R ' expression hydrogen or organic group as replace or unsubstituted aryl and/or alkyl group.For example, the group of connection can comprise hydroxy-acid group, sulfonic acid group, sulfate groups or its salt, as benzene carboxylic acid group, benzene dicarboxylic acid group, benzene tricarbonic acid's group, Phenylsulfonic acid group or its salt.The organic group that connects can also be the derivative of the replacement of any of these material.
Cation group is positively charged organic ion group, and it can generate by forming cationic ionizable substituting group such as protonated amines (cationizable groups).For example, alkyl or aryl amine can be in acidic medium by protonated to form ammonium group-NR ' 2H +, wherein R ' expression organic group as replace or unsubstituted aryl and/or alkyl group.Cation group can also be positively charged organic ion group.Example comprise quaternary ammonium group (NR ' 3 +) and season
Figure GSB00001072687200051
Group (PR ' 3 +).At this, R ' expression hydrogen or organic group as replace or unsubstituted aryl and/or alkyl group.
When modified pigment comprised the pigment of the organic group with connection, organic group can be polymkeric substance.Preferably, polymeric groups comprises above-mentioned ion or ionogen.Therefore, but organic group can be the polymeric groups that comprises one or more negatively charged ion or anionizable group.Example includes, but not limited to poly-acid as the multipolymer of polyacrylic acid, polymethyl acrylic acid, acrylic or methacrylic acid, comprises the styrene-propene acid polymer and contains the hydrolysis derivative of the polymkeric substance of maleic anhydride.Organic group can also be the polymeric groups that comprises one or more positively charged ions or cationizable groups.Example includes, but not limited to the oligopolymer of the polyamine of straight or branched such as polymine (PEI), ethyleneimine (as five vinyl-amines, PEA) and the derivative of polymine.
As mentioned above, in the methods of the invention, polymkeric substance and pigment combinations are to form mixture.This mixture can be that dried forms can be the form of dispersion or suspension maybe, depends on the form for the preparation of its polymkeric substance and pigment.For example, polymkeric substance can be solid form (as powder or wax) or liquid form (as viscosity or non-viscous liq, comprising syrup or oil).In addition, polymkeric substance can be form moisture or non-aqueous polymer solution, suspension, dispersion or emulsion.Preferably, polymkeric substance can be polymers soln form and, especially, comprise the form of aqueous polymers solution of the mixture of water or water and water-miscible solvent such as alcohol.In addition, pigment can be dried forms (as powder, pellet or filter cake) or the moisture or nonaqueous dispersion in liquid or the form of suspension.In addition, pigment can be the form of wet cake, comprises liquid such as the water of about 20-80%, but still is solid or semi-solid form.Preferably, pigment be pigment suspension or dispersion form and, especially, comprise the aqueous pigment suspension of mixture of water or water and water-miscible solvent such as alcohol or the form of dispersion.If polymkeric substance or pigment are the forms that comprises liquid medium, as solution, dispersion or suspension, therefore the gained mixture is similar form so.Perhaps, if polymkeric substance or pigment are not the forms that comprises liquid medium, the gained mixture is solid or semi-solid form so, comprises for example easy mobility or cohesive powders, paste or putty.At last, if polymkeric substance or pigment, but be not both, be the form that comprises liquid medium, the gained mixture can have the liquid or solid form so, depends on the consumption of liquid medium.
Polymkeric substance and pigment can use any technology known in the art or equipment combination, and this depends on the form of the mixture of component and generation.For example, if polymkeric substance and pigment are not that form or the gained mixture with liquid medium is solid or semi-solid form, can use high strength mixing condition.These conditions are well known by persons skilled in the art and can use the various high intensity mixer that are designed for mixing, blend, stirring, homogenize, dispersion and/or compounding material and similar devices and realizing.High intensity mixer can be intermittence, semicontinuous or continuous mixing device, but the relative batch process equipment of continuous mixing device provides economic and actual advantage and generally is preferred.The example of high intensity mixer comprises, but be not limited to list or duplicate rows star mixing tank, twin shaft epicyclic mixer (especially one of them have the zig-zag blade those), mixing screw such as twin-spiral mixer or the conical mixing tank of twayblade, double arm kneading mixer such as Brabender or Farrel mixing tank, this Henschel of high intensity mixer or papenmeir mixing tank, 2 or 3 roller mixing tanks and single or two (two) screw extrusion press.High strength mixing condition also can comprise the low pressure condition of using vacuum and obtaining.
For example, if polymkeric substance and/or pigment are that form and the gained mixture that comprises liquid medium also is this form, can use high shear mixing.Therefore, mixing can be adopted under shear conditions in suitable containers can provide equipment or other device that reduces particle size of grinding or shock action such as liquid shear cavitation to carry out.Different shearing devices can in conjunction with or series connection use, as horizontal medium grinding machine, perpendicular media grinding machine such as masher, ball mill, hammer mill, rotating disk pin formula grinding machine, fluid energy mill, aeropulverizer, acoustic wave device etc.Preferably, high-shear takes place in high pressure fluid crash response device.Other example includes, but not limited to high-pressure homogenizer, rotor stator, partitioning device, impact dispersers (media/ball) etc.
Polymkeric substance and pigment can make up in being enough to produce the temperature and time of desired mixt.Mixing time and temperature depend on a number of factors, and comprise for example kind and the form of pigment, the relative quantity of the kind of polymkeric substance, molecular weight and form and each component.Usually, each component is at about 5 ℃ to about 70 ℃, preferred about 15 ℃ to about 50 ℃ and more preferably from about 20 ℃ to about 30 ℃ temperature, make up.But occurrence temperature raises in the combination step process, and this depends on the kind of used mixing equipment.Mixing time normally about 5 minutes to about 24 hours, preferred about 10 minutes to about 12 hours and more preferably from about 30 minutes to about 2 hours.
Behind the preparation mixture, the inventive method further comprises mixture heating up to the step of about 70 ℃ to 250 ℃ temperature with the formation color compositions.Heating can use any known equipment that the temperature of mixture can be increased to temperature required scope to carry out.Example comprises heating jacket, thermopair, heating bath etc.Also comprise discussed above and can in mixing process, increase high intensity mixer and the high-shear mixer of temperature.Preferably, mixture is heated to about 100 ℃ to 200 ℃ and 140 ℃ to 185 ℃ temperature more preferably from about.In addition, heating can be carried out under inert atmosphere such as nitrogen or argon.
Mixture is heated the enough time to form required color compositions.This time is depended on various factors, comprises kind, reaction scale and the pigment of polymkeric substance and the relative ratios of polymkeric substance.In addition, if mixture is to comprise the pigment of the form of liquid medium or the form that use comprises liquid medium or polymer manufacture, medium also is removed in the heating steps process.Therefore, heating steps also can be the drying step of its medium evaporation and the time that is used for heating to comprise dry this mixture time necessary.In the inventive method embodiment preferred, mixture is heated the enough time so that a large amount of ammonium carboxylic acid salt groups changes into the ammonia that is removed in heat-processed.Typically, mixture is heated about 5 minutes to 5 days, and 1 hour to about 3 days time according to appointment.Any drying means known in the art also can be used for heating steps, comprises for example oven drying, spraying drying and flash distillation.
Polymkeric substance and pigment can be according to various ratio combinations according to the form of each component.For example, if polymkeric substance and pigment all add with the form that does not contain liquid medium, the amount of each component can be preferably in pigment to the weight of polymkeric substance about 5: 1 to 1: 5, more preferably in pigment to about 5: 1 to 1: 1 of the weight of polymkeric substance with most preferably in pigment to the weight of polymkeric substance about 2: 1 to 1: 1.If pigment and/or polymkeric substance are the forms that comprises liquid medium, the amount of each component depends on the concentration of pigment or polymkeric substance.Normally about 0.1% to 25% weight of polymers soln, dispersion, suspension or emulsion concentration, preferably about 1% to 20% weight and more preferably from about 2% to 10% weight.Pigment dispersion or suspension is 1% to 25% weight normally, preferably about 2% to 20% weight and more preferably from about 5% to 15% weight.Added amount or used concentration can be regulated and be made pigment and polymer ratio fall in the above-mentioned scope.
In the methods of the invention, polymkeric substance and pigment combinations to be forming mixture, and with this mixture heating up to form color compositions.The gained color compositions comprises greater than 50%, is preferably greater than 60%, the pigment more preferably greater than 70%.Therefore, color compositions of the present invention is different from polymer composition such as coating, printing ink etc., because these compositions comprise the pigment that is dispersed in the polymkeric substance.Typical coating and ink combination deposits yields comprise coating or the image that is lower than 50% weight pigment.
Although be reluctant to be confined to theory, it is believed that after polymkeric substance and pigment composition heating, polymkeric substance generation chemistry and/or physical change, and surface of pigments is not had other reaction.Therefore, it is believed that the inventive method does not cause pigment and polymer reaction, but polymkeric substance self is transformed.For example, if polymkeric substance comprises the ammonium salt of at least a hydroxy-acid group, it is believed that the ammonium carboxylate groups changes into hydroxy-acid group when heating.Polymkeric substance also can, or individually, the experience crosslinking reaction, wherein the molecular weight of polymkeric substance increases in heat-processed.It is believed that therefore resultant polymer composition comprises pigment and polymkeric substance, this polymkeric substance is different from the polymkeric substance for the preparation of it.Found that polymer content that this method can produce connection is higher than the color compositions of alternative method.
The inventive method can further comprise the step of polymer composition being disperseed to form pigment dispersion.The preferred polymeric compositions is dispersed in the water medium of the mixture that comprises water or water and water-miscible solvent, forms aqueous pigment dispersions thus.If color compositions is formed by the mixture that comprises water medium, this step also can be called the redispersion step and water medium can be identical or different in this case so.Any method for the preparation of pigment dispersion known in the art can be used for this dispersion (or redispersion) step.For example, dispersion can be used the high shear mixing condition to form and can use any aforesaid device or method.Preferable methods comprises use alkali, is used in combination individually or with the high shear mixing condition.For example, water-soluble alkali such as hydroxide reagent can be used for dispersible pigment composition, and described hydroxide reagent is to comprise OH -The alkali of ion comprises sodium hydroxide, potassium hydroxide, lithium hydroxide and ammonium hydroxide.Also can use the mixture of other hydroxide salt and hydroxide reagent.In addition, also can use other in water medium, to produce OH -The alkaline reagents of ion.Example comprises carbonate such as yellow soda ash, supercarbonate such as sodium bicarbonate and alcoholate such as sodium methylate and sodium ethylate.
Therefore, the invention further relates to the aqueous pigment dispersions that comprises above-mentioned color compositions.The consumption of color compositions changes according to the relative quantity of pigment and polymkeric substance, but is enough to produce the aqueous pigment dispersions that comprises about 0.1% to 25% weight pigment.Although aqueous pigment dispersions of the present invention can use minimum additional component preparation, can comprise that also suitable additive to give various performances to aqueous pigment dispersions, comprises the dispersion stabilization of improvement.Other additive can comprise following about inkjet ink composition of the present invention in greater detail those.
Aqueous pigment dispersions of the present invention can be further purified and/or classification is impurity or unwanted dissociant in the dispersion to remove to coexist.For example, aqueous pigment dispersions can for example wash to remove unreacted raw material, by-product salt and other reaction impurities by filtration, combination centrifugal or two kinds of methods.Product also can for example use the known technology of those skilled in the art to separate by evaporation or by filtering and dry the recovery.In addition, use the known ultrafiltration/diafiltration technology of film or ion-exchange to can be used for the purifying dispersion and remove a large amount of dissociated ions and non-required material.Optional counter ion exchange step also can be carried out in purifying process, the counter ion that adopt known ion exchange technique such as ultrafiltration, reverse osmosis, ion exchange column etc. will form an aqueous pigment dispersions part thus exchange or replace with the counter ion of replacing (comprising, as amphiphilic ions).The object lesson of tradable counter ion includes, but not limited to Na +, K +, Li +, NH 4 +, Ca 2+, and Mg 2+
Color compositions of the present invention and aqueous pigment dispersions can be used for various application, include, but are not limited to printing ink, coating, plastics, paper, textiles and rubber product.Especially, they have been found to be used for effectively inkjet ink composition, especially aqueous inkjet ink compositions.
Therefore, the invention still further relates to inkjet ink composition, comprise a) liquid vehicle and b) color compositions of the present invention or aqueous pigment dispersions of the present invention.The inventive method and preparing in greater detail more than preferred pigments composition or aqueous pigment dispersions use.
Usually, inkjet ink composition is by forming as the vehicle of carrier and tinting material such as dyestuff or pigment.Additive and/or solubility promoter can introduce to regulate printing ink, realize desired properties.Preferably, the liquid vehicle for inkjet ink composition of the present invention is that therefore aqueous vehicle and inkjet ink composition are aqueous inkjet ink compositions.Aqueous vehicle can be with above-described identical about the method for organic coloring agent dispersion of preparation modification.
Be used for the color compositions of inkjet ink composition of the present invention or aqueous pigment dispersions with above-mentioned identical, and do not influence the amount existence of the performance of jetted ink so that required image quality (for example, optical density (OD)) to be provided effectively unfriendly.For example, use color compositions or aqueous pigment dispersions so that the inkjet ink composition that comprises based on the amount of about 0.1% to about 20% pigment of ink by weight to be provided usually.Also can use the mixture of tinting material.In addition, use comprise be described in the modified pigment product in the U.S. Patent No. 5,630,868,5,803,959,5,837,045 and 5,922,118 for example prescription also within the scope of the present invention, these patents are all incorporated the present invention into as a reference at this.
Inkjet ink composition of the present invention can form with minimum additional component (additive and/or solubility promoter) and treatment step.But suitable additive also can be introduced in these inkjet ink compositions to give many desired properties, keeps the stability of composition simultaneously.For example, can add tensio-active agent with the colloidal stability of further increase composition.Other additive is well known in the art, and comprises wetting agent, biocide, binding agent, dry promotor, permeate agent etc.The amount of special additive changes according to various factors, but amount is 0% to 40% usually.
In addition, inkjet ink composition of the present invention can further be introduced dyestuff with the modification color balance and regulate optical density (OD).These dyestuffs comprise food dye, FD﹠amp; The derivative of C dyestuff, matching stain, substantive dyestuff, reactive dyestuffs, phthalocyanine sulfonic acid comprises copper phthalocyanine derivative thing, sodium salt, ammonium salt, sylvite, lithium salts etc.
Inkjet ink composition can use as being used for those method purifying and/or classification of above-mentioned color compositions and aqueous pigment dispersions.Like this, unwanted impurity or do not need macrobead can remove to generate the jetted ink with good overall performance.
The present invention further illustrates by following examples, and described embodiment only is exemplary in essence.
Embodiment
The preparation of embodiment 1-4-aqueous pigment dispersions
Following examples are described and are used the inventive method to prepare aqueous pigment dispersions of the present invention.
Embodiment 1
(molecular weight Mw is 8 with 30g Joncryl 683,000-10.000 and acid number is 165 water-soluble phenylethene acrylic copolymer, can derive from Johnson Polymer, Inc.), the mixture of the dense ammonium hydroxide of 12.5mL and 655mL DI water uses Silverson Rotor-Stator Mixer combination, dissolve fully until all solids.In this solution that stirs fast, add 37.5g PY74 as wet cake (20% moisture content can derive from Sun Chemical).The gained mixture at room temperature uses Silverson Rotor-Stator Mixer at 1,000-5 in the high shear mixing condition subsequently, stirs 1 hour under the 000RPM.The gained yellow mixture is poured in the Pyrex furnace pot (about 1/3 is full) and is placed A level (Class A) stove.Mixture heated 18 hours down at 175 ℃ subsequently, formed solid yellow pigment composition thus.
The gained color compositions is cooled to room temperature and makes up with 400mL DI water, 90mL 1M NaOH combination subsequently, and under the high shear mixing condition, use Silverson Rotor-Stator Mixer to disperse subsequently.Be blended in 1,000-5, continued 1 hour under the 000RPM.In this process, make regular check on pH and use other 1M NaOH to be adjusted to greater than 12.5.The gained aqueous pigment dispersions is used Misonix probe sonicator (Misonix Sonicator 3000) sonication subsequently in ice bath, be lower than 180nm until mean volume (mV) particle diameter and (use
Figure GSB00001072687200101
Particle Size Analyzer measures).
Aqueous pigment dispersions use ps hollow fiber uf membrane (aperture: 0.05 micron) and 0.1M NaOH as a supplement liquid by the diafiltration purifying.The solids content of retentate is regulated in whole diafiltration process and is remained on 10%.After the alkali of 10 volumes, liquid make-up becomes DI water and continues diafiltration until the little siemens in electric conductivity＜250 of penetrant.Ultimate density is adjusted to 10% solid.At last, further to use (the Misonix Sonicator 3000) sonication of Misonix probe in ice bath be about 100nm until final mean volume (mV) particle diameter to dispersion.
The performance of gained aqueous yellow pigment dispersion of the present invention provides in following table 1.
Embodiment 2
Aqueous red pigment dispersion of the present invention is used and is similar to embodiment 1 described process preparation, except 103g pigment red 122 filter cake (71% moisture content can derive from Sun Chemical) is used for substituting outside the PY74.The furnace temperature that is used for heating steps is 150 ℃.
The performance of gained aqueous red pigment dispersion of the present invention provides in following table 1.
Embodiment 3
Aqueous blue pigment dispersion of the present invention is used and is similar to embodiment 1 described process preparation, and except the 81g pigment Blue 15: 4 filter cakes (63% moisture content can derive from Sun Chemical) are used for substituting outside the PY74.The furnace temperature that is used for heating steps is 150 ℃.
The performance of gained aqueous red pigment dispersion of the present invention provides in following table 1.
Embodiment 4
The moisture black pigment dispersion of the present invention is used and is similar to embodiment 1 described process preparation, except 30g Black
Figure GSB00001072687200111
700 carbon blacks (BP700 can derive from Cabot Corporation) are used for substituting outside the PY74.The furnace temperature that is used for heating steps is 150 ℃.
The performance of the moisture black pigment dispersion of gained of the present invention provides in following table 1.
Comparative Examples 1
Moisture black pigment dispersion is used and is similar to embodiment 4 described processes preparations, and except after with black pigment and combination of polymers, the gained mixture is in stove outside the heating.Sample is diafiltration after the first sonication step directly.
The performance that gained contrasts moisture black pigment dispersion provides in following table 1.
The performance of aqueous pigment dispersions
The performance of the aqueous pigment dispersions of embodiment 1-4 and Comparative Examples 1 provides in following table 1.
Table 1: the performance of dispersion
Sample UPA?mv Na +(ppm) % connects
Embodiment 1 0.116 6,379 9.2
Embodiment 2 0.0865 13,400 24.7
Embodiment 3 0.1191 12,103 22.4
Embodiment 4 0.1312 13,568 21.8
Comparative Examples 1 0.1393 7,864 14.6
As discussing in above embodiment, particle diameter uses
Figure GSB00001072687200121
Particle Size Analyzer measures and record value is median particle volume diameter (mV).Na ion concentration uses Orion sodium ion selective probe to measure and be recorded as the micrograms of the sodium of every gram solid.Connecting percentage ratio uses TA Instruments TGA Model 2950 to be calculated by thermogravimetric analysis (TGA).Analyze for TGA, sample under nitrogen atmosphere according to following temperature distribution analysis (unless referring else): 10 ℃/minute up to 110 ℃, kept 10 minutes down at 110 ℃, continues heating down up to 800 ℃ and kept 10 minutes down at 800 ℃ at 10 ℃/minute.Percentage ratio connects to be determined by final product is compared with the weight loss of raw material between 110 ℃ and 800 ℃ in the weight loss between 110 ℃ and 800 ℃.
Shown in the result in the table 1, the color compositions of the present invention for preparing with post-heating by the combination of polymers with pigment and the ammonium salt that comprises hydroxy-acid group has the polymkeric substance that is connected of high-content, and produces the aqueous pigment dispersions with good (lower) pigment particle size.The amount expection of the polymkeric substance that connects changes according to kind and the size of used pigment.But two kinds of dispersions (embodiment 4 and Comparative Examples 1 are all used identical black pigment) of relatively using identical type pigment to produce, result clearly illustrate the much higher connection level of using the inventive method, and less particle size dispersion.
The preparation of embodiment 5-8-inkjet ink composition
Inkjet ink composition of the present invention is to use the aqueous pigment dispersions preparation of embodiment 1-4 at prescription shown in the following table 2.
Table 2: ink jet ink formulations:
Component Amount (%)
Aqueous pigment dispersions (3.5 solids basis)
2-Pyrrolidone 7
1,5-pentanediol 7
TriMethylolPropane(TMP) 5
Surfynol?465 0.2％
DI water All the other
Pouring the black ink-jet inks composition of embodiment 8 neutralization of into HP45 box is printed by HP P1000 thermal ink jet printers.Be printed on three kinds of different common paper and carry out: HP Bright White (HPBW), Hammermill Copy Plus (HCP) and Xerox 4024 (4024).The color inkjet inks composition of embodiment 5-7 is printed on the various glossy medias by Canon i550 thermal ink jet printers.Find that each inkjet ink composition printing of the present invention is good, produce the printed images with desirable overall performance.
For example, OD, time of drying, outline-color stain (highlighter smear) and the water dungeon degree of the image of the black ink-jet inks composition printing of assessment use embodiment 8.The result provides in following table 3.
Table 3: the black printing result on various paper types
? HPBW HCP 4024
OD 1.43 0.90 0.85
Time of drying 85-90s 0-5s 5-10s
The outline-color stain 0.488 0.069 0.046
The water dungeon degree Be Be Be
In table 3, refer to time of drying a piece of paper printing ink on the surface of the printed images that nuzzles up is no longer taken place by the time that color shifts, in second.The outline-color stain refers to the OD (mean value of bronsted lowry acids and bases bronsted lowry promotion) of the pigment that shifts in 2 times promotions (highliter) friction process.At last, the water dungeon degree refers to that whether occurring pigment in 1000 microliters of water after printing when dripping on the printed images in 5 minutes under the 45 flows.Result in the table 3 shows that inkjet ink composition of the present invention can be used for producing the printed images with good overall performance.
More than be to provide in order to explain with illustration purpose to the description of the preferred embodiment of the invention.This do not mean that be limit or the present invention is limited to disclosed precise forms.Modification and variation are possible according to above instruction, or enforcement according to the present invention obtains.Select and describe described embodiment to explain principle of the present invention and practical application so that those skilled in the art can be with the present invention with various embodiments and various alternative applications, as the concrete purposes that is suitable for considering.Scope of the present invention is limited by claims and equivalent thereof.

Claims (31)

1. method for preparing color compositions may further comprise the steps:
I) will comprise the polymkeric substance of ammonium salt of at least a hydroxy-acid group and pigment combinations with form mixture and
Ii) heat this mixture to 140 ℃ to 250 ℃ temperature, comprise pigment and be different from color compositions for the preparation of the polymkeric substance of the polymkeric substance of described color compositions with formation.
2. the process of claim 1 wherein that the polymkeric substance for the preparation of described color compositions is the form of aqueous polymers solution.
3. the process of claim 1 wherein that pigment is the form of aqueous pigment suspension or dispersion.
4. the process of claim 1 wherein that polymkeric substance and pigment for the preparation of described color compositions make up under high strength or high shear mixing condition.
5. the process of claim 1 wherein pigment and for the preparation of the polymkeric substance of described color compositions according to pigment and 5: 1 to 1: 5 weight ratio combination for the preparation of the polymkeric substance of described color compositions.
6. the method for claim 5, wherein pigment is 5: 1 to 1: 1 with weight ratio for the preparation of the polymkeric substance of described color compositions.
7. the process of claim 1 wherein the ammonium salt that comprises at least a hydroxy-acid group of at least 10% weight for the preparation of the polymkeric substance of described color compositions.
8. the method for claim 7 wherein comprises the ammonium salt of at least a hydroxy-acid group of at least 20% weight for the preparation of the polymkeric substance of described color compositions.
9. the method for claim 7 wherein comprises the ammonium salt of at least a hydroxy-acid group of at least 30% weight for the preparation of the polymkeric substance of described color compositions.
10. the process of claim 1 wherein that the polymkeric substance for the preparation of described color compositions is ammonium acrylate polymkeric substance or methacrylate polymers.
11. the process of claim 1 wherein that the polymkeric substance for the preparation of described color compositions is styrene-propene acid ammonium polymer or vinylbenzene-methacrylate polymers.
12. the process of claim 1 wherein that mixture uses the spray-dryer drying.
13. the process of claim 1 wherein that pigment comprises blue pigments, black pigment, brown, green pigment, veridian, white pigment, violet pigment, magenta pigment, red pigment, yellow ultramarine or its mixture.
14. a method for preparing aqueous pigment dispersions said method comprising the steps of:
I) will comprise the polymkeric substance of ammonium salt of at least a hydroxy-acid group and pigment combinations forming mixture,
Ii) heat this mixture to 140 ℃ to 250 ℃ temperature, with formation comprise pigment and be different from for the preparation of the color compositions of the polymkeric substance of the polymkeric substance of described color compositions and
Iii) in water medium, disperse this color compositions to form aqueous pigment dispersions.
15. the method for claim 14, wherein color compositions disperses under the high shear mixing condition.
16. the method for claim 14, wherein color compositions disperses by adding alkali.
17. an inkjet ink composition comprises:
A) liquid vehicle; With
B) color compositions, the wherein method preparation of color compositions by may further comprise the steps:
I) will comprise the polymkeric substance of ammonium salt of at least a hydroxy-acid group and pigment combinations with form mixture and
Ii) heat this mixture to 140 ℃ to 250 ℃ temperature, comprise pigment and be different from color compositions for the preparation of the polymkeric substance of the polymkeric substance of described color compositions with formation.
18. the inkjet ink composition of claim 17, wherein the polymkeric substance for the preparation of described color compositions is the form of aqueous polymers solution.
19. the inkjet ink composition of claim 17, wherein pigment is the form of aqueous pigment suspension or dispersion.
20. the inkjet ink composition of claim 17, wherein polymkeric substance and the pigment for the preparation of described color compositions makes up under high strength or high shear mixing condition.
21. the inkjet ink composition of claim 17, wherein pigment and for the preparation of the polymkeric substance of described color compositions according to weight ratio 5: 1 to 1: 5 combination of pigment to polymkeric substance.
22. the inkjet ink composition of claim 17, wherein pigment is 5: 1 to 1: 1 with weight ratio for the preparation of the polymkeric substance of described color compositions.
23. the inkjet ink composition of claim 17 wherein comprises the ammonium salt of at least a hydroxy-acid group of at least 10% weight for the preparation of the polymkeric substance of described color compositions.
24. the inkjet ink composition of claim 23 wherein comprises the ammonium salt of at least a hydroxy-acid group of at least 20% weight for the preparation of the polymkeric substance of described color compositions.
25. the inkjet ink composition of claim 23 wherein comprises the ammonium salt of at least a hydroxy-acid group of at least 30% weight for the preparation of the polymkeric substance of described color compositions.
26. the inkjet ink composition of claim 17, wherein the polymkeric substance for the preparation of described color compositions is ammonium acrylate polymkeric substance or methacrylate polymers.
27. the inkjet ink composition of claim 17, wherein the polymkeric substance for the preparation of described color compositions is styrene-propene acid ammonium polymer or vinylbenzene-methacrylate polymers.
28. the inkjet ink composition of claim 17, wherein mixture uses the spray-dryer drying.
29. the inkjet ink composition of claim 17, wherein pigment comprises blue pigments, black pigment, brown, green pigment, veridian, white pigment, violet pigment, magenta pigment, red pigment, yellow ultramarine or its mixture.
30. the inkjet ink composition of claim 17, wherein liquid vehicle is aqueous vehicle.
31. an inkjet ink composition comprises:
A) liquid vehicle; With
B) aqueous pigment dispersions, the wherein method preparation of aqueous pigment dispersions by may further comprise the steps:
I) will comprise the polymkeric substance of ammonium salt of at least a hydroxy-acid group and pigment combinations forming mixture,
Ii) heat this mixture to 140 ℃ to 250 ℃ temperature, with formation comprise pigment and be different from for the preparation of the color compositions of the polymkeric substance of the polymkeric substance of described color compositions and
Iii) in water medium, disperse this color compositions to form aqueous pigment dispersions.
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US20110060098A1 (en) 2011-03-10
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US8492457B2 (en) 2013-07-23
WO2007014007A2 (en) 2007-02-01
CN101273097A (en) 2008-09-24
WO2007014007A3 (en) 2007-09-27
JP2009503151A (en) 2009-01-29
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US20070021530A1 (en) 2007-01-25
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